The Blue Haired Assistant
by XashXdawnX
Summary: Everything was going well for Ash. He had his high school/college sweetheart and a successful job. However, that's all shattered one random day, sending Ash into turmoil. Can a blue haired assistant help him recover? Can friendship blossom into more?


**XashXdawnX - This is a prequel to Christmas Party Mishaps & Memories. I had this idea after reading over the story once again. This will be about Ash before he met Dawn, once Dawn entered his life, and then catch up to the events of Christmas Party Mishaps & Memories.**

 **Hope you enjoy!**

Ash Ketchum was currently in his apartment kitchen cooking breakfast. He couldn't wait for this weekend. Things were about to change in his life, hopefully for the better.

He couldn't be happier. He was living with his girlfriend since junior year of high school and he had a successful job as a lawyer at one of the best law firms in the area.

"Morning, Mist." he greeted, as his girlfriend walked into the kitchen.

Misty was tall and slim with fiery orange hair that grazed her shoulders when down and greenish blue eyes. She was currently wearing her hair in a messy bun and one of her loose tees.

"Morning," she replied, kissing his cheek and walking over to the coffeemaker.

"I made you breakfast. I have to get going before I'm late. I'll see you tonight."

Ash walked over to her and kissed her cheek. "I love you,"

"Love you, too."

He grabbed the briefcase that was on the counter and left the apartment.

* * *

"Ash! Brock wants to see you." Danica, the front desk attendee said as he walked through the front doors.

"Okay, Danica...thanks. Good morning, by the way." Ash greeted.

"Morning, good luck today!"

"Same to you."

... ... ...

Ash stopped outside of Brock's office and knocked before he opened the door. Brock was sitting behind his desk, but in front of his desk in one of the chairs was a young woman with sapphire blue hair.

"Good morning, Ash. Please take a seat."

"Morning," Ash responded as he sat down in the other chair.

"Ash, I would like you to meet Dawn Berlitz." Brock said.

Ash turned and looked at the woman. She was a few years younger than himself with long sapphire blue hair that was falling behind her shoulders in soft waves and sapphire blue eyes to match. She was wearing a white pencil skirt with a black top and black and white heels.

"It's nice to meet you." he said, extending his hand towards her.

"Likewise." she replied, giving a small smile.

"I mentioned that you were going to get an assistant and Dawn here will be your assistant. She'll help you sort through some cases and do any errands you need. Maybe one day she'll be promoted if she impresses."

Ash nodded his head.

"Well good luck Dawn."

"Thank you for this."

Ash and Dawn stood up and left Brock's office.

"Have you been shown around yet?" Ash questioned as they walked towards where his office was.

"Briefly...I was shown the necessary rooms." Dawn replied.

"Okay, well it's pretty simple really..."

* * *

It had been a few months since Dawn had became Ash's assistant and she was doing quite well. The two got along well and Dawn was just glad that Ash treated her nicely and with respect and not like a servant.

"Hey Dawn?" Ash asked, poking his head into her office.

"Yeah?" she asked, looking up from her computer.

"Could you go grab lunch and a coffee for me?"

"Yeah, no problem. The usual?"

"Yes, please."

Dawn nodded her head and grabbed her purse.

"Thank you, Dawn."

"You're welcome, Ash. I'll be back soon."

... ... ...

Ash got out of his car with takeout in his hands and walked up the stairs to his apartment door.

"Mist?" he called.

No response.

"Mist?"

"Ash!" Misty cried, walking into the room.

"Sorry, I was in the bathroom."

"I brought takeout."

"My hero."

... ... ...

The two were currently cuddled on the couch, watching a movie.

"Ash?" Misty asked.

Ash hummed.

Misty shifted and sat up, grabbing the remote to turn the movie off.

"What's wrong?" Ash asked, now concerned by her behavior.

"I need to talk to you."

"Is everything okay?"

Silence filled the room. Misty looked upset and uncomfortable. Ash was looking at her with concern, waiting for her to speak.

"Mist?"

"I...I can't do this anymore."

Ash stared at her, not quite sure he had heard her correctly.

"What?"

"I can't do this anymore. Ash, I-I don't love you...anymore."

Ash felt physically sick. She didn't love him anymore?

"I...I've felt this way for a while now. Things just aren't what they used to be. We don't get to spend time together anymore...you're working a lot..."

"I'm a lawyer, Mist...I can't help that I have a lot of cases at times."

"I know, but I just...the spark is gone."

"Don't do this..." Ash said, softly.

"I'm not happy anymore, Ash. I can't do this. I just don't love you anymore. I'm sorry,"

"I-I'm going to Gary's..." Ash said, softly.

He felt numb. He looked at Misty to see that she barely looked upset. Meanwhile, his whole world was tumbling out of control. He couldn't understand, but if she wasn't happy he had to let her go to be happy. He loved her and he only wanted her to be happy and now he guessed she needed to find the love that he could no longer provide for her.

He barely even registered walking out of the apartment, getting into his car, and calling Gary. The only thing that broke him from the trance was Gary's voice.

"Ash?"

"I'm coming over."

"You okay?"

"No..."

"Front door will be open. Just walk on in. I'll have some drinks ready."

"Thanks, Gary."

* * *

 _Junior year...prom was approaching and Ash was nervous. He knew who he wanted to ask to go with him, but he also wanted to ask her to be his girlfriend._

 _"What if she says no?" Ash asked._

 _"Ashy Boy, she'll be crazy to say no. She likes you, too. You two have chemistry, but you've been too blind to see it until now." Gary replied._

 _"Shut up, Gary."_

 _"Why must they always travel in packs? How are you suppose to get one alone to ask them?" Ash asked as the approached a group of girls._

 _"Easy, I'll get the others and you get your girl." Gary replied._

 _Ash nodded his head and approached Misty. She was laughing with her friends and stopped upon noticing him._

 _"Hi, Ash." she greeted._

 _"Urm...hey Misty."_

 _"What's up?"_

 _"I was wondering would you maybe...possibly want to go out with me and to prom?"_

 _"You mean be your girlfriend?"_

 _"Yes, I would like you to be my girlfriend and go to prom with you."_

 _"I'd like that."_

 _"Really?"_

 _"Yeah, I've liked you for a while Ash."_

 _Ash chuckled uneasily._

 _"I'll text you the color of my dress and we can discuss plans."_

 _"Okay..."_

* * *

Ash shook his head coming out of the memories. But his mind betrayed him and wondered more down memory lane.

 _College graduation was approaching quickly and Ash and Misty were currently in Ash's room browsing apartments. They planned to move in together once graduation was done._

 _"How about this one?" Ash asked, clicking on one._

 _"Hmm...two bedrooms, one bath, a kitchen, living room, two closets. Oh! It's close to the community pool!" Misty cried._

 _"Want to schedule a tour of this one? So we can see it for ourselves. I think you really like this one since it's close to the pool."_

 _"Please?"_

 _"Of course, I'll call the landlord and get an appointment made. And it's right in our price range, too."_

 _Misty smiled and kissed him before she grabbed her bag to go and study in the library._

* * *

He pulled to a stop outside of Gary's house, got out, and walked straight into the house.

He found Gary in the kitchen, leaning against the island with a glass of liquor in his hand. Another glass was on the island, waiting for Ash.

"What happened?" Gary asked.

Ash walked over to the island and downed the contents in the glass. He instantly knew that it was rum by the burn it left down his throat.

"Misty...she just ended things." he said, staring at the empty glass in his hand.

"What? Why?" Gary asked, pouring some more into Ash's glass.

This time Ash sipped at the drink instead of downing it. He didn't need to get completely wasted, but then at the same time he wanted to.

"She said she didn't love me anymore. She's not happy anymore...she apparently felt this way for a while now. It's almost like she's blaming my work for her unhappiness since we don't spend much time together anymore."

"How can...did she show any signs of ending things?"

Ash shook his head and downed the rest of the rum in his glass.

"Not that I could tell, but I don't know...maybe I was naive and didn't see them..."

Gary was quiet, allowing Ash to just ramble about what happened.

"She said the spark was gone. I mean this morning she seemed fine. When I got back from work...she seemed fine. We were watching a movie, cuddling on the couch and she suddenly turned it off. Next thing I know...it's all over."

"Damn...Ash I don't know what to tell you..."

"Oh and get this. She didn't even look upset during this. But I guess since she doesn't love me anymore, she can't be upset? She was so..." Ash trailed.

He reached for the bottle.

"You may want to slow down some, Ash."

"I would just like to forget..."

Gary nodded his head.

"Can you at least pace yourself?"

"Okay..."

A small silence passed.

"Do you think she could have cheated on me?" Ash asked, breaking the silence.

"I don't think she would do that to you. I would believe she has too much respect for you to do that to you."

"I just don't understand why suddenly end things...I understand she wasn't happy or in love with me anymore...but maybe we could have worked things out."

"Maybe this was meant to happen."

"...Maybe...this just sucks."

* * *

The next morning...

Ash woke up with a splitting headache and groaned at the sunlight that was streaming into the room.

He sat up and was confused as to where he was for a moment, before he remembered everything from the previous night. Misty had broken up with him...he came to Gary's...he got plastered since he wanted to forget.

He walked into the bathroom and found that his eyes were puffy and swollen slightly. He did faintly recall crying at one point during the night...or was it during his sleep? Either way he needed to get ready for work before he was late.

"Gary?" he called.

Nothing.

He glanced at the clock to see that he was going to be cutting it close with being on time.

"Shit..." he muttered.

He didn't have his briefcase. He didn't have his clothes. Nothing for work.

He groaned in frustration and sat down at the end of the bed. How could things be going so well and suddenly take a horrible turn?

"Here you go. I would opt for being late cause you desperately need a shower." Gary said from the doorway.

Ash looked at him to see that he had gotten his work supplies for him.

"Thanks,"

"No problem, I'll let Brock know you'll be running a little late, okay?"

Ash nodded his head and took his things from Gary.

... ... ...

Ash made it to the firm about an hour after when he was suppose to be there.

He walked into his office to find a coffee, a water, and a bottle of aspirin waiting on his desk. Beside those was a pile of neatly, stacked folders. The cases that he had asked Dawn to look over.

He decided that he might as well get caught up with the hour that he had missed.

... ... ...

It was nearing lunch time and he had just finished a conference with one of his clients and was finishing the last bit of paperwork, when his phone went off.

He glanced at it and realized that someone was calling.

He looked at the Caller ID to see Misty's face on the screen. He frowned and answered the call.

"Hello?"

 _"Hey, I was just calling to check up on you. Also to tell you that I'm packing up. I'll be moved out by the end of the week."_

"Wait, what?"

 _"I'm packing my things. There's no reason for me to stay in the apartment anymore."_

"I-You stay. I can move out. I'm sure Gary would lend me his spare room."

 _"I'm going to move and stay with my sisters."_

"Oh..."

 _"Thank you for the offer though. I hope you can continue with the rent. I'll leave my share for this month's rent. Also I'm going to have my name taken off the lease once I'm moved out completely."_

"Okay..."

 _"Are you going to be staying at Gary's until I'm out?"_

"I'm not sure, honestly."

 _"I think it would be better that way. I can get out of your hair quicker if I'm here by myself."_

"Misty...I don't..."

 _"No, Ash. It's over...I'm sorry."_

The call was ended before he could say anything else. He sighed and set his phone on the desk.

He put his head in his hands and tried to stop the tears that he felt building, but he couldn't. He didn't want her to moveout...sure they had broken up, but this was final. She had made it to where there was no room for disucssion, no chance or hope to work things out. The small flciker of hope that Ash had had now been snuffed out at her words. She didn't want this nor was she going to explain anything else. Ash had so many questions that were left unanswered and he wasn't going to get the answers he desired. She had told him to stay away until she was all moved out.

 _I don't want to continue living there...there's too many memories..._

He lost the battle and the tears fell.

He was so lost in his thoughts that he didn't hear the knock on his door. He startled when he heard the door close.

"S-Sorry..." Dawn stuttered. "I knocked, but you didn't answer, but Gary said you were here. I was just going to ask what you wanted for lunch?"

Ash wiped at his face and tried to conceal his emotions. He didn't need to be questioned.

"I think I'm actually going to go home." he responded.

"Are you okay?" she questioned.

"I'm fine," he muttered.

"I know it's not my place, but if you ever need to talk to someone, I'm here to listen. I consider you my friend even though I work for you."

Ash nodded his head.

"Can I get you anything for lunch?"

"I'm not hungry."

Dawn opened her mouth, but closed it. She gave a stiff nod and walked out of Ash's office.

Ash sighed and grabbed one of the folders.

... ... ...

Thirty minutes had passed and he was barely making any progress. His mind was elsewhere and he couldn't focus.

A knock on the door made him look up.

"It's open,"

Dawn walked into the room with a to go bag.

"Here you go, your usual."

"I-"

"I may not know what's going on with you, but you still need to eat. I'm going to eat in here to make sure you eat. So sorry to burst you bubble, but you're getting company for lunch today." Dawn replied as she sat down on the opposite side of his desk with her salad.

Ash looked at her and then the to go bag that was in front of him. He sighed in defeat.

* * *

Ash groaned and grabbed his phone that was ringing.

"Hello?"

 _"Ash, look I wouldn't be calling if this wasn't important."_

"What's going on Gary?"

 _"If you don't stop missing work for "personal days" you're about to lose your job."_

"Really?"

 _"Yes! Ash, you're going to lose your job if you don't stop with the pity party."_

"I'm not having a pity party."

 _"Dude, ever since Misty ended things you've been acting strange. You barely won the cases you were assigned and you're one of the best. Brock's worried about you, but he also sees that if you don't get your shit together you're getting booted. Everyone can see that something's wrong and I'm the only one that knows what's going on, but you won't talk to me. If you won't talk to me, talk to someone. Ash, you can't lose your job. If you don't do something, I'm going to take measures into my own hands."_

"I know. I know. It's just hard for me to focus on things."

 _"Okay...well just remember what I said. We can't afford to lose you and I know you don't want to lose your job either."_

"Yeah..."

 _"Just come back tomorrow, okay?"_

"I guess..."

 _"Otherwise you're out."_

"Lovely..."

The call ended and Ash sighed.

He knew that skipping work and calling for personal days was the wrong way to go about things, but he was trying to get things back to normal. He had been trying to find a new apartment and work on some cases that he had, but all he had managed to do was drink, browse some apartments, and then end up frustrated as his mind wondered back to Misty. He kept trying to work and focus on anything other than her, but he was still hurt. She was his first love and to have things end so suddenly and unexpectedly had damaged him.

He couldn't lose his job, but right now he wasn't himself or at the top of his game. He was almost like himself when he first started. Unsure of everything and unfocused.

He sighed and ran his hand through his hair.

He looked at his apartment and made a face. He needed to clean. Things were a mess and he himself needed a shower.

... ... ...

After his shower he was dressed casually and decided to start cleaning.

Maybe just maybe this could help clear his head and he could feel like himself again.

He plugged his iPod up to a speaker and blasted music, before he started cleaning his apartment.

He was just heading to the front door with a bag of garbage when there was a knock.

He opened the door to find Dawn.

"Dawn?"

"Umm...hey?"

Ash held up a finger and went to pause the music before returning to Dawn at the door.

"What are you doing here?" he asked.

"I know it's not my place, but Gary asked me to come see you. He umm...I don't know really. He told me that you needed someone that you didn't really know to talk to...I-"

"Oh...umm yeah. I know what he's talking about. Umm...come on in. Sorry that it's a mess, I was right in the middle of cleaning."

Dawn stepped into the apartment.

"I could help you, if you would like."

"Oh no, that-"

"Looks like you could need some help. Ash, like I told you before, I consider you a friend. Let me help, okay?"

"Okay..."

* * *

Once Ash's apartment was cleaned the two were sitting in the living room. Ash had told her about what was going on with him, why he was being short, missing work, angry at times, and why he had been sad. Dawn listened to everything that he said and after he was done she spoke some, before she grabbed the laptop that was on the table.

"I actually know of an apartment complex that has quite a few apartments for sell. Maybe it'll be useful." she said as she typed in the complex name and handed Ash the laptop.

"Thanks, Dawn."

"No problem, just know that I'll be here okay? And please don't lose your job, I like working with you and I don't want to take your spot."

"What?"

"Brock mentioned that I could take your spot if you didn't return. I politely declined the offer. I would rather earn my spot, rather than get it because of someone losing their job."

"Thanks...I'll be there tomorrow. I promise,"

* * *

Two years had passed and Dawn had managed to become a lawyer and was no longer Ash's assistant. Her and Ash had become close friends and on Mondays and Fridays they would have lunch together.

It was quickly approaching the annual Christmas party and Ash was nervous, but excited.

Over the time that he had spent with Dawn and her being there for him through his rough time, he had developed feelings for her. He was hoping to tell her tonight at the party, if she came that is, but she had always been at the parties.

He was dressed in a black button up shirt, a tie, and khaki pants. He laughed as he remembered that Gary would be wearing a ugly Christmas sweater since he had lost a bet.

Ash was currently driving and while he was driving he was talking to Gary on the phone.

 _"Dude, just relax. I'm sure she likes you, too."_

"What if she doesn't? I mean she used to work for me and through that she became one of my closest friends. What if I ruin our friendship?"

 _"Don't think about the what ifs. I still need to meet her. I may work in the same office as her, but I've rarely seen her. I spoke to her once over the phone, but I haven't properly met her."_

"She's amazing."

 _"If I didn't know any better I would say you love her."_

"No, I just like her."

... ... ...

Once arriving to the party, Ash cringed at the sight. Like always the decorations were overboard. He made his way to the bar to get a drink and ended up finding Gary leaning against the bar, sipping a drink.

Ash chuckled at the sight of Gary in the ugly Christmas sweater.

"Hey, Ashy Boy!" he greeted.

"Hey," Ash greeted and ordered a drink.

... ... ...

Ash and Gary were currently in the crowd of people, talking to the fellow co-workers.

"So do you see Dawn, yet?" Gary asked.

Ash scanned the crowd and shook his head.

"Not that I can see."

"A shame. I can't wait to meet her. After everything you've told me about her, she seems lovely."

"She is..."

Gary looked down at his sweater and shook his head.

"I can't believe I lost the bet and had to wear this damn sweater." he said, but he noticed that Ash's attention was drawn to something behind him.

Gary turned around and saw two women approaching. One with sapphire blue hair in a long sleeve dark blue dress that was a v cut. The other was a brunette in a red sweater dress with white leggings.

This had to be Dawn and a friend of hers.

"Hi, Ash..." the bluenette greeted.

"Hey Dawn, you look nice." Ash greeted with a small smile.

"Thanks. Enjoying the party?"

"Eh, it's the same as every year. But I have to say it's a lot better now that I actually have another friend here."

Dawn smiled. "Oh! This is my best friend, Leaf Green. I forced her to come..."

The brunette, now known as Leaf smiled. "It's nice to finally meet you, Ash. I've heard a lot about you."

This caused Dawn to glare at Leaf.

Ash chuckled. "I've heard a lot about you, too."

Gary cleared his throat, causing Dawn's attention to shift to him.

"I'm Gary Oak,"

"Nice to meet you." Dawn said.

Leaf took a sip of her drink and Dawn eyed her friend.

"Leaf?"

"Sorry, nice to meet you." she replied, glancing at Gary.

* * *

Ash and Dawn had really hit it off and had managed to find a table to sit at and talk.

"So what made you want to become a lawyer?" Ash asked.

"Oh...it's not a happy story honestly. I mainly just wanted to be able to help people in their time of need."

Ash nodded his head.

"Enough talk about work...what's some of your hobbies?" Dawn asked.

"I love music. I actually have a guitar at home that I play and write songs, too."

"Do you sing?"

"Not really..."

"Oh! You do sing! That's really cool, Ash. You'll have to play me a song one day."

Ash chuckled, "Maybe."

Dawn smiled. "So if you had the chance to go back would you major in music instead?"

Ash was quiet for a moment. "Yes and no."

"Yes and no?"

"Yes, because I think it would of been really fun. No, because I feel like it would have taken some of the passion I have for music away, but also because if I had done that I wouldn't have met you."

Dawn blushed slightly and nodded her head.

"I think if I could have picked anything else to go into...I would have chosen fashion design or writing for a fashion magazine. I really love fashion."

"Interesting."

Ash and Dawn eventually ended up going to Ash's apartment to continue getting to know one another and ended up falling asleep talking to one another.

* * *

The next morning...

Ash woke up, stiff and disoriented to begin with and he was confused as to what was on his chest. He looked down and saw Dawn's head on his chest and he realized that he was holding her.

They had fallen asleep talking to one another last night. He hadn't managed to tell her how he felt about her either...

Maybe he could today?

"Oh...sorry. I didn't mean to fall asleep last night." Dawn said as she sat up, rubbing her eyes.

"It's fine. I didn't mean to either. Are you hungry?" Ash asked.

Dawn nodded her head.

"I'll cook some breakfast. Umm...you're welcomed to use the shower if need be."

"Thanks,"

"Umm...Dawn?"

Dawn looked at him and waited.

"If you want to change out of your dress, you can grab a shirt if you want."

"Umm...thanks Ash. Could you pick one for me?"

"Sure, I can set it on the bed and I'll be here cooking. So when you get out just come down here."

Dawn nodded her head.

... ... ...

Ash had just finished cooking when Dawn walked into the kitchen. Ash had picked out a black button up and it came down far enough that Dawn was covered, but damn did she look beautiful. She had pulled her hair into a messy bun on her head and her makeup was removed from her face. She looked beautiful.

"Breakfast smells amazing." she said, breaking Ash from his thoughts.

"Hope it tastes as good as it smells." Ash replied.

"I'm sure it does. Thank you," Dawn responded as she took the plate offered to her.

They ate in a comfortable silence, occasionally talking once in a while.

Once they were finished Ash cleared the table and loaded the dishes into the dishwasher.

"Well I probably need to head back home. I also need to check on Leaf and make sure she got home okay last night." Dawn said.

"Wait!" Ash cried, seeing that she was about to leave.

"I can um drive you."

"Thanks,"

Ash walked over towards her since his keys were hanging up where she was.

"Dawn?"

"Yes?"

"...Can I ask you something?"

"Of course, Ash."

"May I kiss you?"

Dawn looked at him in shock for a moment, before she gave a soft reply.

"Yes,"

Ash was shocked that she had said yes. He held back the smile that threatened to show on his face. He stepped closer to Dawn and cupped her face before pressing his lips to her, tentatively. She responded by pushing herself on her toes to kiss him back, which in turn, gave him the encouragement to put a little more emotion behind the kiss.

Once they parted, Ash had his forehead resting against Dawn's.

"Dawn...I've liked you for a while now. Would you be my girlfriend?" Ash asked, softly and looking into her eyes.

She smiled and nodded her head. "I'd love that."

Ash then smiled and Dawn pecked his lips. Ash grabbed his keys from the hook by her head and Dawn grabbed his hand.

 **Please R &R**


End file.
